Light emitting device
Abstract
A light emitting device comprising an anode, a cathode, a first light emitting layer between the anode and the cathode, and a second light emitting layer between the anode and the cathode is provided. The first light emitting layer comprises a metal complex represented by formula (1): In formula (1), M 1 represents an iridium atom, n 1 represents an integer of 1 or more, n 2 represents an integer of 0 or more, n 1 +n 2 is 2 or 3, ring R 1A represents a triazole ring containing a nitrogen atom, E 1 , E 11A , E 12A , and a carbon atom, ring R 2 represents an aromatic hydrocarbon ring, E 1 , E 2 , E 11A , and E 12A each represent a nitrogen atom, R 11A and R 12A represent an aryl group, R 13A represents an aryl group, A 1 -G 1 -A 2 represents an anionic bidentate ligand, A 1 and A 2 each represent a nitrogen atom, and G 1 represents a single bond.
Claims
exact text as granted — not AI-modified1 . A light emitting device, comprising:
an anode; a cathode; a first light emitting layer provided between the anode and the cathode; and a second light emitting layer provided between the anode and the cathode, wherein the first light emitting layer comprises a metal complex represented by formula (1):
wherein
M 1 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,
n 1 represents an integer of 1 or more, n 2 represents an integer of 0 or more, and n 1 +n 2 is 2 or 3,
when M 1 is a rhodium atom or an iridium atom, n 1 +n 2 is 3, and when M 1 is a palladium atom or a platinum atom, n 1 +n 2 is 2,
the ring R 1A represents a triazole ring or a diazole ring constituted of a nitrogen atom, E 1 , E 11A , E 12A , and a carbon atom,
the ring R 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of the substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of the ring R 2 , they may be the same or different,
E 1 represents a carbon atom, and E 2 , E 11A , and E 12A each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E 2 , E 11A and E 12A , they may be the same or different at each occurrence,
R 11A and R 12A each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R 11A and R 12A , they may be the same or different at each occurrence; R 11A and R 12A may be bonded to each other to form a ring together with the atoms to which they are bonded; and R 11A and an optional substituent of the ring R 2 may be bonded to each other to form a ring together with the atoms to which they are bonded,
when E 11A is a nitrogen atom, R 11A may be present or absent, and when E 12A is a nitrogen atom, R 12A may be present or absent,
R 13A represents an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups each may have a substituent; when there are a plurality of R 13A , they may be the same or different; and R 12A and R 13A may be bonded to each other to form a ring together with the atoms to which they are bonded, and
A 1 -G 1 -A 2 represents an anionic bidentate ligand, A 1 and A 2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms each may be atoms constituting a ring; G 1 represents a single bond or an atomic group constituting the bidentate ligand together with A 1 and A 2 ; and when there are a plurality of A 1 -G 1 -A 2 , they may be the same or different.
2 . The light emitting device according to claim 1 , wherein the second light emitting layer comprises
a metal complex represented by formula (2):
wherein
M 2 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,
n 3 represents an integer of 1 or more, n 4 represents an integer of 0 or more, and n 3 +n 4 is 2 or 3; when M 2 is a rhodium atom or an iridium atom, n 3 +n 4 is 3; and when M 2 is a palladium atom or a platinum atom, n 3 +n 4 is 2,
E 4 represents a carbon atom or a nitrogen atom,
the ring L 1 represents a 6-membered aromatic heterocyclic ring, which may have a substituent; when there are a plurality of the substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of the ring L 1 , they may be the same or different,
the ring L 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of the substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of the ring L 2 , they may be the same or different,
an optional substituent of the ring L 1 and an optional substituent of the ring L 2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and
A 3 -G 2 -A 4 represents an anionic bidentate ligand, A 3 and A 4 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms each may be atoms constituting a ring; G 2 represents a single bond or an atomic group constituting the bidentate ligand together with A 3 and A 4 ; and when there are a plurality of A 3 -G 2 -A 4 , they may be the same or different.
3 . The light emitting device according to claim 1 , wherein the second light emitting layer comprises at least one selected from the group consisting of:
a polymer compound comprising a constitutional unit having a group formed by removing from a metal complex represented by formula (2) one or more hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the metal complex; and a crosslinked product of the polymer compound
wherein
M 2 represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,
n 3 represents an integer of 1 or more, n 4 represents an integer of 0 or more, and n 3 +n 4 is 2 or 3; when M 2 is a rhodium atom or an iridium atom, n 3 +n 4 is 3; and when M 2 is a palladium atom or a platinum atom, n 3 +n 4 is 2,
E 4 represents a carbon atom or a nitrogen atom,
the ring L 1 represents a 6-membered aromatic heterocyclic ring, which may have a substituent; when there are a plurality of the substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of the ring L 1 , they may be the same or different,
the ring L 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings each may have a substituent; when there are a plurality of the substituents, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded; and when there are a plurality of the ring L 2 , they may be the same or different,
an optional substituent of the ring L 1 and an optional substituent of the ring L 2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and
A 3 -G 2 -A 4 represents an anionic bidentate ligand, A 3 and A 4 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms each may be atoms constituting a ring; G 2 represents a single bond or an atomic group constituting the bidentate ligand together with A 3 and A 4 ; and when there are a plurality of A 3 -G 2 -A 4 , they may be the same or different.
4 . The light emitting device according to claim 3 , wherein the constitutional unit is a constitutional unit represented by formula (1B), a constitutional unit represented by formula (2B), a constitutional unit represented by formula (3B), or a constitutional unit represented by formula (4B):
L c n c1 M 1B (1B)
wherein M 1B represents a group formed by removing from the metal complex represented by the formula (2) one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the metal complex, L C represents an oxygen atom, a sulfur atom, —N(R A )—, —C(R B ) 2 —, —C(R B )═C(R B )—, —C≡C—, an arylene group, or a divalent heterocyclic group, and these groups each may have a substituent; R A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; R B represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; the plurality of R B may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded; and when there are a plurality of L C , they may be the same or different, and n c1 represents an integer of 0 or more;
wherein
M 1B represents the same meaning as described above,
L d and L e each independently represent an oxygen atom, a sulfur atom, —N(R A )—, —C(R B ) 2 —, —C(R B )═C(R B )—, —C≡C—, an arylene group, or a divalent heterocyclic group, and these groups each may have a substituent; R A and R B represent the same meaning as described above; and when there are a plurality of L d and L e , they may be the same or different at each occurrence,
n d1 and n e1 each independently represent an integer of 0 or more, and the plurality of n d1 may be the same or different, and
Ar lM represents an aromatic hydrocarbon group or a heterocyclic group, and these groups each may have a substituent;
L d n d1 M 2B L d n d1 (3B)
wherein
L d and n d1 represent the same meaning as described above, and
M 2B represents a group obtained by removing from the metal complex represented by the formula (2) two hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the metal complex;
wherein
L d and n d1 represent the same meaning as described above, and
M 3B represents a group obtained by removing from the metal complex represented by the formula (2) three hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the metal complex.
5 . The light emitting device according to claim 2 , wherein the metal complex represented by formula (2) is a metal complex represented by formula (2-B):
wherein
M 2 , n 3 , n 4 , and A 3 -G 2 -A 4 represent the same meaning as described above,
E 11B , E 12B , E 13B , E 14B , E 21B , E 22B , E 23B , and E 24B each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E 11B , E 12B , E 13B , E 14B , E 21B , E 22B , E 23B , and E 24B , they may be the same or different at each occurrence; when E 11B is a nitrogen atom, R 11B is absent; when E 12B is a nitrogen atom, R 12B is absent, when E 13B is a nitrogen atom, R 13B is absent; when E 14B is a nitrogen atom, R 14B is absent; when E 21B is a nitrogen atom, R 21B is absent; when E 22B is a nitrogen atom, R 22B is absent; when E 23B is a nitrogen atom, R 23B is absent; and when E 24B is a nitrogen atom, R 24B is absent,
R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B , and R 24B each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic ring, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R 11B , R 12B , R 13B , R 14B R 21B , R 22B , R 23B , and R 24B , they may be the same or different at each occurrence; and R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , R 14B and R 21B , R 21B and R 22B , R and R 23B , and R 23B and R 24B each may be bonded to each other to form a ring together with the atoms to which they are bonded,
the ring L 1B represents a pyridine ring or a pyrimidine ring constituted of a nitrogen atom, a carbon atom, E 11B , E 12B , E 13B , and E 14B , and
the ring L 2B represents a benzene ring, a pyridine ring, or a pyrimidine ring constituted of two carbon atoms, E 21B , E 22B , E 23B , and E 24B .
6 . The light emitting device according to claim 5 , wherein the metal complex represented by formula (2-B) is a metal complex represented by formula (2-B1), a metal complex represented by formula (2-B2), a metal complex represented by formula (2-B3), a metal complex represented by formula (2-B4), or a metal complex represented by formula (2-B5):
wherein
M 2 , n 3 , n 4 , A 3 -G 2 -A 4 , R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B , and R 24B represent the same meanings as described above,
n 31 and n 32 each independently represent an integer of 1 or more, and n 31 +n 32 is 2 or 3; when M 2 is a rhodium atom or an iridium atom, n 31 +n 32 is 3; and when M 2 is a palladium atom or a platinum atom, n 31 +n 32 is 2, and
R 15B , R 16B , R 17B , and R 18B each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R 15B , R 16B , R 17B , and R 18B , they may be the same or different at each occurrence; R 15B and R 16B , R 16B and R 17B , and R 17B and R 18B each may be bonded to each other to form a ring together with the atoms to which they are bonded.
7 . The light emitting device according to claim 1 , wherein the metal complex represented by formula (1) is a metal complex represented by formula (1-A):
wherein
M 1 , n 1 , n 2 , ring R 1A , E 1 , E 11A , E 12A , R 11A , R 12A , R 13A , and A 1 -G 1 -A 2 represent the same meanings as described above,
the ring R 2A represents a benzene ring, a pyridine ring, or a pyrimidine ring constituted of two carbon atoms, E 21A , E 22A , E 23A , and E 24A ,
E 21A , E 22A , E 23A , and E 24A each independently represent a nitrogen atom or a carbon atom; when there are a plurality of E 21A , E 22A , E 23A , and E 24A , they may be the same or different at each occurrence; when E 21A is a nitrogen atom, R 21A is absent; when E 22A is a nitrogen atom, R 22A is absent; when E 23A is a nitrogen atom, R 23A is absent; and when E 24A is a nitrogen atom, R 24A is absent, and
R 21A , R 22A , R 23A , and R 24A each represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups each may have a substituent; when there are a plurality of R 21A , R 22A , R 23A , and R 24A , they may be the same or different at each occurrence; R 21A and R 22A may be bonded to each other to form a ring together with the atoms to which they are bonded; R 22A and R 23A may be bonded to each other to form a ring together with the atoms to which they are bonded; R 23A and R 24A may be bonded to each other to form a ring together with the atoms to which they are bonded; and R 11A and R 21A may be bonded to each other to form a ring together with the atoms to which they are bonded.
8 . The light emitting device according to claim 7 , wherein the metal complex represented by formula (1-A) is a metal complex represented by formula (1-A1), a metal complex represented by formula (1-A2), a metal complex represented by formula (1-A3), or a metal complex represented by formula (1-A4):
wherein M 1 , n 1 , n 2 , R 11A , R 12A , R 13A , R 21A , R 22A , R 23A , R 24A , and A 1 -G 1 -A 2 represent the same meanings as described above.
9 . The light emitting device according to claim 1 , wherein R 13A is an aryl group which may have a substituent.
10 . The light emitting device according to claim 1 , wherein the first light emitting layer further comprises a compound represented by formula (H-1):
Ar H1 L H2 n H2 L H1 n H1 L H2 n H2 n H3 Ar H2 (H-1)
wherein Ar H1 and Ar H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent, n H1 and n H2 each independently represent 0 or 1; when there are a plurality of n H1 , they may be the same or different; and the plurality of n H2 may be the same or different; n H3 represents an integer of 0 or more, L H1 represents an arylene group, a divalent heterocyclic group, or a group represented by —[C(R H11 ) 2 ]n H11 -, and these groups each may have a substituent; when there are a plurality of L H1 they may be the same or different; n H11 represents an integer of 1 or more and 10 or less; R H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of R H11 may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded, and L H2 represents a group represented by —N(-L H21 -R H21 )—; when there are a plurality of L H2 , they may be the same or different; L H21 represents a single bond, an arylene group, or a divalent heterocyclic group, and these groups each may have a substituent; R H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups each may have a substituent.
11 . The light emitting device according to claim 1 , wherein the first light emitting layer and the second light emitting layer are adjacent to each other.
12 . The light emitting device according to claim 1 , wherein the second light emitting layer is provided between the anode and the first light emitting layer.
13 . The light emitting device according to claim 2 , wherein at least one selected from the group consisting of the ring L 1 and the ring L 2 has as a substituent a group represented by formula (D-A), (D-B) or (D-C):
wherein
m DA1 , m DA2 , and m DA3 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent,
Ar DA1 , Ar DA2 , and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , Ar DA2 and Ar DA3 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of T DA may be the same or different;
wherein
m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 , and m DA7 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent; the plurality of G DA may be the same or different,
Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; the plurality of T DA may be the same or different;
Ar DA1 m DA1 T DA (D-C)
wherein
m DA1 represents an integer of 0 or more,
Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 they may be the same or different, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent.
14 . The light emitting device according to claim 5 , wherein at least one selected from the group consisting of R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B , and R 24B is a group represented by formula (D-A), (D-B) or (D-C):
wherein
m DA1 , m DA2 , and m DA3 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent,
Ar DA1 , Ar DA2 , and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , Ar DA2 , and Ar DA3 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of T DA may be the same or different;
wherein
m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 , and m DA7 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent; the plurality of G DA may be the same or different,
Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; the plurality of T DA may be the same or different;
Ar DA1 m DA1 T DA (D-C)
wherein
m DA1 represents an integer of 0 or more,
Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , they may be the same or different, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent.
15 . The light emitting device according to claim 6 , wherein at least one selected from the group consisting of R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B , and R 24B is a group represented by formula (D-A), (D-B) or (D-C):
wherein
m DA1 , m DA2 , and m DA3 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent,
Ar DA1 , Ar DA2 , and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , Ar DA2 , and Ar DA3 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of T DA may be the same or different;
wherein
m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 , and m DA7 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent; the plurality of G DA may be the same or different,
Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; the plurality of T DA may be the same or different;
Ar DA1 m DA1 T DA (D-C)
wherein
m DA1 represents an integer of 0 or more,
Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 they may be the same or different, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent.
16 . The light emitting device according to claim 3 , wherein at least one selected from the group consisting of the ring L 1 and the ring L 2 has as a substituent a group represented by formula (D-A), (D-B) or (D-C):
wherein
m DA1 , m DA2 , and m DA3 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent,
Ar DA1 , Ar DA2 , and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , Ar DA2 , and Ar DA3 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; and the plurality of T DA may be the same or different;
wherein
m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 , and m DA7 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups each may have a substituent; the plurality of G DA may be the same or different,
Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 , and Ar DA7 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent; the plurality of T DA may be the same or different;
Ar DA1 m DA1 T DA (D-C)
wherein
m DA1 represents an integer of 0 or more,
Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups each may have a substituent; and when there are a plurality of Ar DA1 they may be the same or different, and
T DA represents an aryl group or a monovalent heterocyclic group, and these groups each may have a substituent.Join the waitlist — get patent alerts
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